Cheshire Community YMCA Harvest Trail Race and Y Cup Relay
- Date Wed 16th September 2026 - Wed 21st October 2026
- Time 9:45AM EDT
- Location Cheshire, Connecticut
- Price Free - $41.28
- Races 3 races
- Distances 5km
Event summary
Get ready for an exciting community event at the Cheshire Community YMCA Harvest Trail Race and Y Cup Relay, taking place from September 16 to October 21, 2026, in the scenic Naugatuck Valley of Cheshire. This vibrant event will feature an all-ages run around the historic Ives Farm, where participants can enjoy the beauty of the fields and trails while supporting local initiatives. The race will kick off with a FREE Pumpkin Dash for kids aged 6 and under at 9:45 AM, followed by the 5K run starting at 10:00 AM and the Y Cup Relay at 10:05 AM.
Join in on the family-friendly festivities that include pumpkin decorating, face painting, Halloween mask making, games, live music, and a fall-themed photo booth. This event not only promises a fun-filled day for everyone but also supports the vital work of the YMCA and the revitalization efforts of the Cheshire Land Trust at Ives Farm. Don't miss this chance to enjoy a beautiful day outdoors while making a positive impact in your community!
Join in on the family-friendly festivities that include pumpkin decorating, face painting, Halloween mask making, games, live music, and a fall-themed photo booth. This event not only promises a fun-filled day for everyone but also supports the vital work of the YMCA and the revitalization efforts of the Cheshire Land Trust at Ives Farm. Don't miss this chance to enjoy a beautiful day outdoors while making a positive impact in your community!
Organiser's Description
The Cheshire Community YMCA and Cheshire Land Trust are partnering on a race around historic Ives Farm. This all-ages run will wind through the fields and trails on the property, with the start and finish line located at the beautifully restored barn. Proceeds from this event will support the work that the YMCA does in the Cheshire community as well as the revitalization plans that the Cheshire Land Trust has for the Ives Farm property.
* Prior to the race there will be a FREE Pumpkin Dash for kids 6 years old and younger.
* Family friendly activities include pumpkin decorating, face painting, Halloween mask making, games, live music and a fall theme photo booth
Pumpkin Dash Start: 9:45AM
5K Start: 10:00AM
Y Cup Relay Start: 10:05AM
* Prior to the race there will be a FREE Pumpkin Dash for kids 6 years old and younger.
* Family friendly activities include pumpkin decorating, face painting, Halloween mask making, games, live music and a fall theme photo booth
Pumpkin Dash Start: 9:45AM
5K Start: 10:00AM
Y Cup Relay Start: 10:05AM
Races
-
5K Trail Race
Incl. $3.28 Fee & Custom Harvest Trail Race Hat
Sat 24th October 2026 (10:00AM EDT)
$41.28
This is a 5k trail race with varied terrain and slight elevation which winds through groomed wooded paths and open fields - perfect for the road runner wanting to try a trail run. It's also a good opportunity for an experienced trail runner to do some speed work. -
Y Cup Relay
Incl. $2.02 Fee & Custom Harvest Trail Race Hat
Sat 24th October 2026 (10:05AM EDT)
$19.02
Teams of 3 elementary school students will each run one mile of the 5K course. Teams from all grades will compete for their team to determine which school wins the prestigious Y Cup for the 26-27 school year. -
Pumpkin Dash
Incl. Finisher Medal
Sat 24th October 2026 (9:45AM EDT)
Free
A free race for children 6yr and younger on the dirt path around the historic Ives Farm barn. Young runners will end the dash by running through the same race finish line as all other racers!
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1585 Cheshire St., Cheshire, 06410, CT, United States
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Cheshire Community YMCA Harvest Trail Race and Y Cup Relay
